Exploiting enzymatic dynamic reductive kinetic resolution (DYRKR) in stereocontrolled synthesis

Gregory A. Applegate, David B Berkowitz

Research output: Contribution to journalReview article

40 Citations (Scopus)

Abstract

Over the past two decades, the domains of both frontline synthetic organic chemistry and process chemistry have seen an increase in crosstalk between asymmetric organic/organometallic approaches and enzymatic approaches to stereocontrolled synthesis. This review highlights the particularly auspicious role for dehydrogenase enzymes in this endeavor, with a focus on dynamic reductive kinetic resolutions (DYRKR) to "deracemize" building blocks, often setting two stereocenters in so doing. The scope and limitations of such dehydrogenase-mediated processes are overviewed, as are future possibilities for the evolution of enzymatic DYRKR.

Original languageEnglish (US)
Pages (from-to)1619-1632
Number of pages14
JournalAdvanced Synthesis and Catalysis
Volume357
Issue number8
DOIs
StatePublished - May 1 2015

Fingerprint

Oxidoreductases
Kinetics
Organometallics
Crosstalk
Enzymes
Organic Chemistry

Keywords

  • asymmetric synthesis
  • biocatalysis
  • dehydrogenase enzymes
  • deracemization
  • dynamic kinetic resolution

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

Exploiting enzymatic dynamic reductive kinetic resolution (DYRKR) in stereocontrolled synthesis. / Applegate, Gregory A.; Berkowitz, David B.

In: Advanced Synthesis and Catalysis, Vol. 357, No. 8, 01.05.2015, p. 1619-1632.

Research output: Contribution to journalReview article

@article{f3bffb266cf24dfe8119fec573dea088,
title = "Exploiting enzymatic dynamic reductive kinetic resolution (DYRKR) in stereocontrolled synthesis",
abstract = "Over the past two decades, the domains of both frontline synthetic organic chemistry and process chemistry have seen an increase in crosstalk between asymmetric organic/organometallic approaches and enzymatic approaches to stereocontrolled synthesis. This review highlights the particularly auspicious role for dehydrogenase enzymes in this endeavor, with a focus on dynamic reductive kinetic resolutions (DYRKR) to {"}deracemize{"} building blocks, often setting two stereocenters in so doing. The scope and limitations of such dehydrogenase-mediated processes are overviewed, as are future possibilities for the evolution of enzymatic DYRKR.",
keywords = "asymmetric synthesis, biocatalysis, dehydrogenase enzymes, deracemization, dynamic kinetic resolution",
author = "Applegate, {Gregory A.} and Berkowitz, {David B}",
year = "2015",
month = "5",
day = "1",
doi = "10.1002/adsc.201500316",
language = "English (US)",
volume = "357",
pages = "1619--1632",
journal = "Advanced Synthesis and Catalysis",
issn = "1615-4150",
publisher = "Wiley-VCH Verlag",
number = "8",

}

TY - JOUR

T1 - Exploiting enzymatic dynamic reductive kinetic resolution (DYRKR) in stereocontrolled synthesis

AU - Applegate, Gregory A.

AU - Berkowitz, David B

PY - 2015/5/1

Y1 - 2015/5/1

N2 - Over the past two decades, the domains of both frontline synthetic organic chemistry and process chemistry have seen an increase in crosstalk between asymmetric organic/organometallic approaches and enzymatic approaches to stereocontrolled synthesis. This review highlights the particularly auspicious role for dehydrogenase enzymes in this endeavor, with a focus on dynamic reductive kinetic resolutions (DYRKR) to "deracemize" building blocks, often setting two stereocenters in so doing. The scope and limitations of such dehydrogenase-mediated processes are overviewed, as are future possibilities for the evolution of enzymatic DYRKR.

AB - Over the past two decades, the domains of both frontline synthetic organic chemistry and process chemistry have seen an increase in crosstalk between asymmetric organic/organometallic approaches and enzymatic approaches to stereocontrolled synthesis. This review highlights the particularly auspicious role for dehydrogenase enzymes in this endeavor, with a focus on dynamic reductive kinetic resolutions (DYRKR) to "deracemize" building blocks, often setting two stereocenters in so doing. The scope and limitations of such dehydrogenase-mediated processes are overviewed, as are future possibilities for the evolution of enzymatic DYRKR.

KW - asymmetric synthesis

KW - biocatalysis

KW - dehydrogenase enzymes

KW - deracemization

KW - dynamic kinetic resolution

UR - http://www.scopus.com/inward/record.url?scp=84930226757&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84930226757&partnerID=8YFLogxK

U2 - 10.1002/adsc.201500316

DO - 10.1002/adsc.201500316

M3 - Review article

C2 - 26622223

AN - SCOPUS:84930226757

VL - 357

SP - 1619

EP - 1632

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

SN - 1615-4150

IS - 8

ER -